Holiday rentals in Old Windsor

5* Boutique Hse Nr Windsor Castle, Ascot & London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, beautiful bathrooms, abundant art and character; the properties look onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Cosy Cabin Retreat, 1–5 guests, 5 mins to Windsor

The Cosy Cabin is a peaceful retreat, ideal for couples or families up to 5. With two double bedrooms, a modern shower room, and comfortable open-plan lounge/kitchen/diner. Enjoy WiFi, Sky and Netflix, or explore nearby: Windsor Castle (5 mins), Legoland (10 mins), Thorpe Park (15 mins), Heathrow (20 minutes) and London under an hour by train. Perfect for romantic getaways and family breaks. Please note the access is through our utility room from a separate entrance into the garden to the cabin.

Wellness Escape by River: Sauna, Pool, Hot Tub

Tucked away in nature, this serene retreat offers two cosy bedrooms and a single bathroom, creating a peaceful and intimate escape. Complete with a private sauna, hot tub, and cold plunge pool, it provides a rejuvenating sanctuary perfect for couples or small groups seeking ultimate relaxation and tranquillity. Welcome to your ultimate riverside retreat! This stunning two-bedroom haven blends natural beauty with serene comfort, offering an unforgettable escape from the everyday. Step inside to

Gorgeous Self-Contained Wooden Cabin - Old Windsor

Beautiful and spacious self-contained log cabin comfortably sleeps 2-4. 1 king size bed, 1 small double sofa bed & 1 king size day bed (lounge). Shower/toilet, lounge and kitchenette. Close to Heathrow (7.4 miles / 15 mins) Great access to Windsor (2.4 miles). Close to a bus stop if needed. 2.5 miles to Runneymede where the Magna Carta was signed. Easy access to Ascot and Legoland The cabin is in the owner's garden. Friendly labrador included so please only book if comfortable around dogs!

The Potting Shed

The Potting Shed, is a characterful & cosy self contained annex that can sleep 1-4 people. Benefiting from a private sheltered courtyard garden for dining or just a morning coffee. Ample off street parking on a gated drive. Overlooking horse fields, the property is close to Windsor Castle, Legoland, river walks, Windsor Great Park, Saville Gardens, Runnymede & easy access into London & Heathrow by train, bus or car. Within 40 mins to central London, Oxford or Warner Bros. Harry Potter world.

Stylish Studio-Walk to Windsor/Eton/Thames/Parking

Welcome to Crail Cottage in Datchet. Surrounded by beautiful greenery, there is plenty of wildlife and the River Thames is just behind the house. Take a walk to Windsor and Eton via the home park or the riverside. You can even walk to Eton through the school grounds from here. Our little studio is freshly decorated and welcomes you to stay. There is a new addition which is a King size bed with Hypnos mattress that will guarantee you a good night sleep. Perfect to relax after a busy day.

2 Bedroom Luxury Cottage (Secure & Quiet)

This charming Cottage is located in the picturesque Village of Englefield Green. Just four miles from Windsor Castle, three miles from Wentworth Golf Course and six miles from Ascot Race Course. Heathrow Airport if just six miles away. 300 metres further down the lane is The Royal Air Force Memorial and below that, on National Trust grounds that skirts the River Thames is the Magna Carta Memorial. The Royal Holloway University is a ten minute stroll across the Village.

4-bed dog-friendly retreat w/ hot tub & garden

Welcome to a characterful four-bedroom home set within the historic Old Windsor Tapestries factory grounds. - Sleeps 9 | 4 bedrooms | 5 beds | 2.5 baths - Private hot tub (£150/stay) - open daily 8AM-9PM, all year round - Fenced backyard w/ BBQ, outdoor dining & communal garden access - Full kitchen w/ Bertozzoni double oven & dining table seats 10 - 48" HDTV w/ Netflix, fast wifi (73 Mbps) & dedicated workspace - Dog-friendly | free parking (x2) | keypad self check-in

River Thames near Windsor, Heathrow & London

Our home sits on the beautiful river Thames in Wraysbury near Windsor. The river runs past the end of the garden. There is a large west facing terrace, from the master bedroom. There is a large living room, kitchen and dinning room. 3 double bedrooms. There's parking for 2 cars in the garden. Windsor, Windsor castle and Lego land are about 20mins away my car. From Wraysbury station you can get into London Waterloo in 42mins. Heathrow is only 15mins drive away.

Luxury 2 bedroom cottage

Luxury Cottage at Hayley Green A charming, character-filled retreat for up to 4 guests in a peaceful semi-rural setting. Designed for comfort and relaxation, it’s ideal for couples, families, or friends. Enjoy a well-stocked library if you prefer to stay in. Perfectly located: 6 mins to Lapland Ascot 9 mins to Legoland 11 mins to Ascot 16 mins to Windsor & Wentworth 30 mins to Henley-on-Thames Under 1 hour by train to London via nearby Bracknell station

The Ultimate Couples Retreat | 30 Mins from London

This countryside retreat is the perfect romantic escape, just a 35 minute taxi/train ride minutes from London. Unwind in your private luxury hot tub, sip on a complimentary bottle Champagne under the stars, and wake up to breathtaking views of rolling fields and wildlife. Our handcrafted shepherd’s hut blends rustic charm with modern comfort, offering a king-sized stargazing bed, a cozy fire-lit deck, and a luxury bathroom, all set in a peaceful meadow.

Windsor Great * Snug * Private Annexe with Parking

*stylish private annexe with off street parking for one car. * self contained studio attached to our family home. * suitable for up to 2 people only. * ideal for both work travellers (key box ) and tourists. * approx 21 m2 *quiet, leafy "Boltons" area. * 15\20 mins stroll to town centre and Castle. * 10 mins stroll to Long Walk and Great Park. * 5 mins cycle to Windsor Great Park cycle path. * local shop and pub 5-10 mins walk.